Pyridine → 3-Methoxy-N-(3-methoxyphenyl)aniline

HRID 1631201Notes

Reaction equation

HRID 1631201 reaction equation
N1C=CC=CC=1.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12].[CH3:16][O:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1>C(Cl)Cl>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([NH:12][C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([O:17][CH3:16])[CH:23]=2)[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 108243-MethoxyanilineHCID 2734370(3-Methoxyphenyl)boronic acid

Product 1

HCID 158359053-Methoxy-N-(3-methoxyphenyl)aniline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cupric acetate (2.1 mmol) and pyridine (0.25 ml) were added to a vigorously stirred solution of 3-methoxyaniline (1 mmol) and 3-methoxyphenylboronic acid (2 mmol) in dry methylene chloride (3.5 ml), under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 72 h (the progress of the reaction was monitored by TLC). N-(3-Methoxyphenyl)-3-methoxyaniline (3c) was isolated by direct flash chromatography of the crude reaction mixture following preabsorption on silica gel. Yield (3c): 25%; EI-MS 229 (M+) [Lit.: Urgaonkar, S.; Verkade, J. G. J. Org. Chem. 2004, 69, 9135-9142].

Sources & evidence

ORD record
ord-eb033ca3c97a4ef5bd15753d5fd3cf81
Source dataset
uspto-grants-2014_07
Patent number
US08791163B2

Reaction notes

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